This chapter explores the opportunities and challenges of utilising blockchain technology to enhance compliance monitoring, regulatory compliance, and due diligence. Blockchain technology may offer the tools needed to usher sophisticated businesses into a new technological era, but ideas about how blockchain technologies fit into current compliance regimes continue to evolve. When new and fundamentally transformative technology meets traditional ways of thinking, there tend to be contradictions to our schema, and the revelation of possibilities is not entirely apparent. Thus, this chapter will attempt to discuss new possibilities of blockchain in the compliance monitoring, regulatory compliance, and due diligence functions. Attention will be given to six possible advantages of using blockchain technology in the compliance function of an organisation: (1) transparency, (2) immutability, (3) real-time availability of information, (4) security, (5) uniqueness, and (6) proof of compliance. This chapter will also discuss challenges to using blockchain technologies and conclude with suggestions.